Iminoacetic acid amides and their use as pest control agents

ABSTRACT

Iminoacetamides of the formula (I) ##STR1## in which A represents a single bond or optionally substituted alkylene, 
     Q represents oxygen or sulphur, 
     R 1  represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, 
     R 2  represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, 
     R 3  represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, 
     R 4  represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl 
     a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.

This appln is a 371 of PCT/EP96/04345 Oct. 7, 1996.

The invention relates to novel iminoacetamides, to a process for theirpreparation and to their use as pesticides.

Novel compounds of the general formula (I) have been found ##STR2## inwhich A represents a single bond or optionally substituted alkylene, Qrepresents oxygen or sulphur,

R¹ represents respectively optionally substituted cycloalkyl,cycloalkenyl, aryl or heterocyclyl,

R² represents respectively optionally substituted alkyl, alkenyl,alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl,

R³ represents hydrogen or respectively optionally substituted alkyl,alkenyl, alkinyl or cycloalkyl,

R⁴ represents respectively optionally substituted cycloalkyl,cycloalkenyl, aryl or heterocyclcyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, including when combinedwith hetero atoms, as in alkoxy, alkylthio or alkylamino, are in eachcase straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as,for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenylor naphthyl, in particular phenyl.

Heterocyclyl represents saturated or unsaturated and aromaticring-shaped compounds in which at least one ring member is a heteroatom, i.e. an atom other than carbon. If the ring contains more than onehetero atom, these may be identical or different. Preferred hetero atomsare oxygen, nitrogen or sulphur.

Ring-shaped compounds optionally combine with further carbocyclic orheterocyclic, fused or bridged rings to form a polycyclic ring system.Preference is given to mono- or bicyclic ring systems, in particular tomono- or bicyclic aromatic ring systems.

Cycloalkyl represents saturated carbocyclic ring-shaped compounds whichtogether with further carbocyclic, fused or bridged rings may form apolycyclic ring system.

Cycloalkenyl represents carbocyclic ring-shaped compounds which containat least one double bond and which together with further carbocyclic,fused or bridged rings optionally form a polycyclic ring system.

Finally, it was found that the novel iminoacetamides of the generalformula (I) have very strong fungicidal activity.

The compounds according to the invention may be present as mixtures ofdifferent possible isomeric forms, in particular of stereoisomers, suchas, for example, E and Z, threo and erythro, and optical isomers. Whatis described and claimed includes both the E and the Z isomers, and alsothe threo and erythro and the optical isomers and any mixtures of theseisomers.

The invention preferably provides compounds of the formula (I) in which

A represents a single bond or represents alkylene having 1 to 6 carbonatoms which is optionally mono- or polysubstituted by identical ordifferent substituents, the possible substituents preferably beingselected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

respectively straight-chain or branched, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties;

cycloalkyl having 3 to 6 carbon atoms;

and aryl or heterocyclyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different substituents from halogenand/or straight-chain or branched alkyl having 1 to 4 carbon atomsand/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms.

Q represents oxygen or sulphur,

R¹ represents aryl, cycloalkyl or cycloalkenyl having 3 to 7 carbonatoms, or heterocyclyl having 3 to 12 ring members, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents, the possible substituents preferably being selected fromthe list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbonatoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 8 carbonatoms in the individual alkyl moieties;

respectively doubly attached alkylene or dioxyalkylene having in eachcase 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by halogen and/or straight-chain or branched alkylhaving 1 to 4 carbon atoms and/or straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio,

each of which is optionally mono- or polysubstituted by identical ordifferent substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms.

R² represents alkyl having 1 to 4 carbon atoms, alkenyl or alkinylhaving in each case 2 to 4 carbon atoms, each of which is optionallymono- or polysubstituted by identical or different substituents from thegroup consisting of halogen, cyano, hydroxyl, amino, C₁ -C₄ -alkoxy, C₁-C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl and C₁ -C₄ -alkylsulphonyl (eachof which is optionally substituted by halogen) and optionallysubstituted phenyl,

or represents aryl, cycloalkyl or cycloalkenyl having 3 to 7 carbonatoms, or heterocyclyl having 3 to 12 ring members, each of which ismono- or polysubstituted by identical or different substituents, thepossible substituents preferably being selected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbonatoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 8 carbonatoms in the individual alkyl moieties;

respectively doubly attached alkylene or dioxyalkylene having in eachcase 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms,

R³ represents hydrogen or alkyl having 1 to 4 carbon atoms,

R⁴ represents aryl, cycloalkyl or cycloalkenyl having 3 to 8 carbonatoms, or heterocyclyl having 3 to 12 ring members, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents, the possible substituents preferably being selected fromthe list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms;

respectively straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

respectively straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonylhaving in each case 1 to 6 carbon atoms and 1 to 13 identical ordifferent halogen atoms;

respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms;

respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties;

respectively doubly attached alkylene or dioxyalkylene having in eachcase 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms;

cycloalkyl having 3 to 6 carbon atoms;

and aryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio,

each of which is optionally mono- or polysubstituted by identical ordifferent substituents from

halogen, cyano and/or straight-chain or branched alkyl having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkyl having 1 to 4 carbonatoms and 1 to 9 identical or different halogen atoms

and/or straight-chain or branched alkoxy or alkylthio having 1 to 4carbon atoms

and/or straight-chain or branched halogenoalkoxy or halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 9 identical or different halogenatoms

and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms.

The invention in particular provides compounds of the formula (I) inwhich

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-,2,2- or 2,3-butylene or 1,1-, 1,2- or 1,3-(2-methylpropylene), each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, cyano andmethoxy,

Q represents oxygen or sulphur,

R¹ represents respectively optionally mono- to trisubstitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl,furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl,quinolyl, pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl,tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl ormorpholinyl, the possible substituents preferably being selected fromthe list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

phenyl, benzyl, phenoxy, benzyloxy, each of which is optionallysubstituted by the abovementioned substituents;

R² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl orpropargyl or allyl or represents respectively optionally mono- totrisubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl,benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl,pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl,pyrrolidinyl, piperidinyl or morpholinyl, the possible substituentspreferably being selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

or represents benzyl which is substituted the abovementionedsubstituents,

R³ represents hydrogen or represents methyl or ethyl,

R⁴ represents optionally mono- to trisubstituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, phenyl, naphthyl, furyl,benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl,isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl,quinolyl, pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl,tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl ormorpholinyl, the possible substituents preferably being selected fromthe list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl,

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Particular preference is given to compounds of the formula (I) in which

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-,2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3-(2-methylpropylene), each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, cyano andmethoxy,

Q represents oxygen or sulphur,

R¹ represents respectively optionally mono- to hexasubstitutedcyclobutyl, cyclopentyl or cyclohexyl, preferred substituents beingthose listed below;

X represents respectively optionally mono- to trisubstituted phenyl,naphthyl, furyl, benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl,tetrahydrofuryl or perhydropyranyl, the possible substituents preferablybeing selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl; cyclopropyl,cyclopentyl, cyclohexyl; phenyl, phenoxy, benzyloxy, each of which isoptionally substituted by the abovementioned substituents;

R² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,allyl,

or represents respectively optionally mono- to hexasubstitutedcyclobutyl, cyclopentyl or cyclohexyl, preferred substituents beingthose listed below;

or represents respectively optionally mono- to trisubstituted phenyl,naphthyl, furyl, benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl,tetrahydrofuryl or perhydropyranyl, the possible substituents preferablybeing selected from the list below:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- or i-propyl,

or represents benzyl which is substituted the abovementionedsubstituents,

R³ represents hydrogen or represents methyl,

R⁴ represents respectively optionally mono- to hexasubstitutedcyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, preferredsubstituents being those listed below;

represents respectively optionally mono- to trisubstituted phenyl,naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl, benzothienyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl,thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl, pyrazinyl,oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl,piperidinyl or morpholinyl, the possible substituents preferably beingselected from the list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl;

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl;

cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

A very particularly preferred group of compounds according to theinvention are those compounds of the formula (I) in which

A represents a single bond or represents methylene, 1,1-ethylene,1,2-ethylene, 1,1-propylene, 1,2-propylene, 1,3-propylene or2,2-propylene,

Q represents oxygen,

R¹ represents phenyl, thienyl or furanyl, each of which is optionallymono- or disubstituted by bromine, chlorine, fluorine, nitro,methylsulphonyl, phenyl, phenyloxy, benzyloxy, cyclopropyl, cyclohexyl,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl,n-heptyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy and/ormethylthio, or represents phenyl which is substituted by 3,4-methylene-and ethylenedioxo, propane-1,3-diyl and butane-1,4-diyl, each of whichis optionally substituted by fluorine, or represents naphthyl,benzofuranyl or benzothienyl,

R² represents methyl or ethyl, represents n- or i-propyl, represents n-,i-, s- or t-butyl, allyl, cyclopentyl, cyclohexyl or representsoptionally chlorine-, methyl- or methoxy-substituted phenyl or benzyl,

R³ represents hydrogen or methyl,

R⁴ represents cyclohexyl or optionally mono- to trisubstituted phenyl,thienyl, furyl, benzofuryl, benzothienyl, pyridyl, pyrimidinyl,naphthyl, quinolyl, the possible substituents preferably being selectedfrom the list below:

fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl,carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, trifluoromethyl, trifluoroethyl,difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, difluorochloromethylthio,trifluoromethylthio, trifluoromethylsulphinyl ortrifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino,dimethylamino, diethylamino, acetyl, propionyl, acetyloxy,methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl,

respectively doubly attached trimethylene (propane-1,3-diyl),tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,methyl, trifluoromethyl, ethyl, n- and i-propyl.

Of very particular interest are compounds of the formula (I) in whichthe radical R¹ represents phenyl which is unsubstituted or substitutedin position 3 and/or 4, or represents thienyl or furanyl which isunsubstituted or substituted in position 4 and/or 5, the substituentsbeing selected from the abovementioned group, in particular chlorine,bromine, fluorine, nitro, methylsulphonyl, phenyl, phenoxy, benzyloxy,cyclopropyl, cyclohexyl, methyl, ethyl, n-, i-propyl, n-, i-, s-,t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, methylthio,trifluoromethyl and trifluoromethoxy, or phenyl which is substituted by3,4-methylene- and ethylenedioxo, propane-1,3-diyl and butane-1,4-diyl,each of which is optionally substituted by fluorine, or benzofuranyl,benzothienyl or naphthyl which is substituted in position 2.

Particular preference is also given to compounds of the formula (I) inwhich R⁴ represents phenyl which is substituted by methoxy in positions3 and 4.

The abovementioned general or preferred definitions of a radical applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

These definitions of a radical can be combined with each other asdesired, that is to say combinations between the ranges stated forpreferred compounds are also possible.

Specific preferred compounds are listed in the tables below:

                  TABLE 1                                                         ______________________________________                                                                      (Ia)                                                                            #STR3##                                          -                                                                          Compound No. R.sup.5       R.sup.6                                            ______________________________________                                        Ia-1         hydrogen      hydrogen                                             Ia-2  4-chloro hydrogen                                                       Ia-3  4-fluoro hydrogen                                                       Ia-4  4-bromo hydrogen                                                        Ia-5  4-methyl hydrogen                                                       Ia-6  4-ethyl hydrogen                                                        Ia-7  4-iso-propyl hydrogen                                                   Ia-8  4-n-propyl hydrogen                                                     Ia-9  4-n-butyl hydrogen                                                      Ia-10 4-iso-butyl hydrogen                                                    Ia-11 4-tert-butyl hydrogen                                                   Ia-12 4-sec-butyl hydrogen                                                    Ia-13 4-methoxy hydrogen                                                      Ia-14 4-ethoxy hydrogen                                                       Ia-15 4-methylthio hydrogen                                                   Ia-16 4-trifluoromethyl hydrogen                                              Ia-17 3-chloro hydrogen                                                       Ia-18 3-fluoro hydrogen                                                       Ia-19 3-bromo hydrogen                                                        Ia-20 3-methyl hydrogen                                                       Ia-21 3-ethyl hydrogen                                                        Ia-22 3-iso-propyl hydrogen                                                   Ia-23 3-n-propyl hydrogen                                                     Ia-24 3-n-butyl hydrogen                                                      Ia-25 3-iso-butyl hydrogen                                                    Ia-26 3-tert-butyl hydrogen                                                   Ia-27 3-sec-butyl hydrogen                                                    Ia-28 3-methoxy hydrogen                                                      Ia-29 3-ethoxy hydrogen                                                       Ia-30 3-methylthio hydrogen                                                   Ia-31 3-trifluoromethyl hydrogen                                              Ia-32 3,4-dichloro hydrogen                                                   Ia-33 3,4-difluoro hydrogen                                                   Ia-34 3,4-dibromo hydrogen                                                    Ia-35 3,4-dimethyl hydrogen                                                   Ia-36 3,4-diethyl hydrogen                                                  Ia-37        --O--CH.sub.2 --O--*                                               Ia-38 --O--CN.sub.2 --CN.sub.2 --O--*                                         Ia-39 --O--CF.sub.2 --O--*                                                    Ia-40 --O--CF.sub.2 --CF.sub.2 --O--*                                         Ia-41 --(CH.sub.2).sub.3 --*                                                  Ia-42 --(CH.sub.2).sub.4 --*                                                Ia-43        3-methoxy     4-methoxy                                            Ia-44 3-ethoxy 4-ethoxy                                                       Ia-45 3-methylthio 4-methylthio                                               Ia-46 3-trifluoromethyl 4-trifluoromethyl                                     Ia-47 3-chloro 4-methyl                                                       Ia-48 4-chloro 3-methyl                                                       Ia-49 3-chloro 4-methoxy                                                      Ia-50 4-chloro 3-methoxy                                                      Ia-51 3-chloro 4-ethyl                                                        Ia-52 4-chloro 3-ethyl                                                        Ia-53 3-methoxy 4-ethoxy                                                      Ia-54 4-methoxy 3-ethoxy                                                      Ia-55 3-methyl 4-methoxy                                                      Ia-56 4-methyl 3-methoxy                                                      Ia-57 3-methyl 4-ethyl                                                        Ia-58 4-methyl 3-ethyl                                                        Ia-59 3-methoxy 4-ethyl                                                       Ia-60 4-methoxy 3-ethyl                                                       Ia-61 4-nitro hydrogen                                                        Ia-62 4- hydrogen                                                              methylsulphonyl                                                              Ia-63 4-phenoxy hydrogen                                                      Ia-64 4-phenyl hydrogen                                                       Ia-65 4-benzyloxy hydrogen                                                    Ia-66 4-pentyl hydrogen                                                       Ia-67 4-hexyl hydrogen                                                        Ia-68 4-heptyl hydrogen                                                       Ia-69 4-cyclopropyl hydrogen                                                  Ia-70 4-cyclohexyl hydrogen                                                 ______________________________________                                         *In each case attached in positions 3 and 4                              

                  TABLE 2                                                         ______________________________________                                                                      (Ib)                                                                            #STR4##                                          -                                                                          Compound No. R.sup.5       R.sup.6                                            ______________________________________                                        Ib-1         hydrogen      hydrogen                                             Ib-2  4-chloro hydrogen                                                       Ib-3  4-fluoro hydrogen                                                       Ib-4  4-bromo hydrogen                                                        Ib-5  4-methyl hydrogen                                                       Ib-6  4-ethyl hydrogen                                                        Ib-7  4-iso-propyl hydrogen                                                   Ib-8  4-n-propyl hydrogen                                                     Ib-9  4-n-butyl hydrogen                                                      Ib-10 4-iso-butyl hydrogen                                                    Ib-11 4-tert-butyl hydrogen                                                   Ib-12 4-sec-butyl hydrogen                                                    Ib-13 4-methoxy hydrogen                                                      Ib-14 4-ethoxy hydrogen                                                       Ib-15 4-methylthio hydrogen                                                   Ib-16 4-trifluoromethyl hydrogen                                              Ib-17 5-chloro hydrogen                                                       Ib-18 5-fluoro hydrogen                                                       Ib-19 5-bromo hydrogen                                                        Ib-20 5-methyl hydrogen                                                       Ib-21 5-ethyl hydrogen                                                        Ib-22 5-iso-propyl hydrogen                                                   Ib-23 5-n-propyl hydrogen                                                     Ib-24 5-n-butyl hydrogen                                                      Ib-25 5-iso-butyl hydrogen                                                    Ib-26 5-sec-butyl hydrogen                                                    Ib-27 5-tert-butyl hydrogen                                                   Ib-28 5-methoxy hydrogen                                                      Ib-29 5-ethoxy hydrogen                                                       Ib-30 5-methylthio hydrogen                                                   Ib-31 5-trifluoromethyl hydrogen                                              Ib-32 4-chloro 5-chloro                                                       Ib-33 4-fluoro 5-fluoro                                                       Ib-34 4-bromo 5-bromo                                                         Ib-35 4-methyl 5-methyl                                                       Ib-36 4-ethyl 5-ethyl                                                         Ib-37 4-methoxy 5-methoxy                                                     Ib-38 4-trifluoromethyl 5-trifluoromethyl                                     Ib-39 4-chloro 5-methyl                                                       Ib-40 5-chloro 4-methyl                                                     ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                                      (Ic)                                                                            #STR5##                                          -                                                                          Compound No. R.sup.5       R.sup.6                                            ______________________________________                                        Ic-1         hydrogen      hydrogen                                             Ic-2  4-chloro hydrogen                                                       Ic-3  4-fluoro hydrogen                                                       Ic-4  4-bromo hydrogen                                                        Ic-5  4-methyl hydrogen                                                       Ic-6  4-ethyl hydrogen                                                        Ic-7  4-iso-propyl hydrogen                                                   Ic-8  4-n-propyl hydrogen                                                     Ic-9  4-n-butyl hydrogen                                                      Ic-10 4-iso-butyl hydrogen                                                    Ic-11 4-tert-butyl hydrogen                                                   Ic-12 4-sec-butyl hydrogen                                                    Ic-13 4-methoxy hydrogen                                                      Ic-14 4-ethoxy hydrogen                                                       Ic-15 4-methylthio hydrogen                                                   Ic-16 4-trifluoromethyl hydrogen                                              Ic-17 5-chloro hydrogen                                                       Ic-18 5-fluoro hydrogen                                                       Ic-19 5-bromo hydrogen                                                        Ic-20 5-methyl hydrogen                                                       Ic-21 5-ethyl hydrogen                                                        Ic-22 5-iso-propyl hydrogen                                                   Ic-23 5-n-propyl hydrogen                                                     Ic-24 5-n-butyl hydrogen                                                      Ic-25 5-iso-butyl hydrogen                                                    Ic-26 5-sec-butyl hydrogen                                                    Ic-27 5-tert-butyl hydrogen                                                   Ic-28 5-methoxy hydrogen                                                      Ic-29 5-ethoxy hydrogen                                                       Ic-30 5-methylthio hydrogen                                                   Ic-31 5-trifluoromethyl hydrogen                                              Ic-32 4-chloro 5-chloro                                                       Ic-33 4-fluoro 5-fluoro                                                       Ic-34 4-bromo 5-bromo                                                         Ic-35 4-methyl 5-methyl                                                       Ic-36 4-ethyl 5-ethyl                                                         Ic-37 4-methoxy 5-methoxy                                                     Ic-38 4-trifluoromethyl 5-trifluoromethyl                                     Ic-39 4-chloro 5-methyl                                                       Ic-40 4-methyl 4-methyl                                                     ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                      (Id)                                                                            #STR6##                                          -                                                                          Compound No.        R.sup.1                                                   ______________________________________                                        Id-1                2-naphthyl                                                  Id-2 2-benzofuranyl                                                           Id-3 2-benzothienyl                                                         ______________________________________                                    

Table 5

Compounds Ia-1 to Id-3 corresponding to the formulae Ia, Ib, Ic and Idwhere the 3,4-dimethoxyphenyl group (generally denoted R⁴) has beenreplaced by one of the following trisubstituted phenyl radicals:substituents: 3,4,5-trimethoxy; 3,4,5-trichloro; 3,4,5-trimethyl.

Furthermore, it has been found that the novel iminoacetamides of thegeneral formula (I) are obtained when carboxylic acid derivatives of thegeneral formula (II) ##STR7## in which R¹, R² and Q are each as definedabove and

T represents hydroxyl, halogen or alkoxy,

are reacted with an amine of the general formula (III), ##STR8## inwhich R³, R⁴ and A are each as defined above

or with a hydrogen halide thereof

if appropriate in the presence of an acid acceptor, if appropriate inthe presence of a condensing agent, if appropriate in the presence of acatalyst and if appropriate in the presence of a diluent.

Formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the processaccording to the invention. In this formula (II), (Q, R¹ and R²) eachpreferably have in particular those meanings which have already beenindicated in connection with the description of the compounds of theformula (I) according to the invention as preferred or as particularlypreferred for (Q, R¹ and R²); T preferably represents alkoxy having 1 to4 carbon atoms, in particular represents methoxy or ethoxy, representshydroxyl or chlorine.

The starting materials of the formula (II) are known and/or can beprepared by known processes (cf. for example, Tetrahedron 1971, 3431-6).

Formula (III) provides a general definition of the amines further to beused as starting materials. In this formula (II), R³, R⁴ and A eachpreferably have in particular those meanings which have already beenindicated in connection with the description of the compounds of theformula (I) according to the invention as preferred or as particularlypreferred for R³, R⁴ and A.

The starting materials of the formula (III) are known organic chemicalsfor synthesis and/or can be prepared by methods known per se.

If appropriate, the process according to the invention is carried out inthe presence of a suitable acid acceptor. Suitable as acid acceptors areall conventional inorganic or organic bases. These include, for example,alkaline earth metal or alkali metal hydrides, hydroxides, amides,alkoxides, acetates, carbonates or bicarbonates, such as, for example,sodium hydride, sodium amide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammoniumhydroxide, sodium acetate, potassium acetate, calcium acetate, ammoniumacetate, sodium carbonate, potassium carbonate, potassium bicarbonate,sodium bicarbonate or ammonium carbonate, and tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylanilin,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU).

If appropriate, the process according to the invention is carried out inthe presence of a suitable condensing agent. Suitable condensing agentsare all condensing agents which are conventionally used for suchamidation reactions. Examples include acid halide formers such asphosgene, phosphorus tribromide, phosphorus trichloride, phosphoruspentachloride, phosphorus oxychloride or thionyl chloride; anhydrideformers such as ethyl chloroformate, methyl chloroformate ormethanesulphonyl chloride; carbodiimides, such asN,N'-dicyclohexylcarbodiimide (DCC), or other conventional condensingagents, such as phosphorus pentoxide, polyphosphoric acid,N,N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine/carbon tetrachloride.

If appropriate, the process according to the invention is carried out inthe presence of a diluent. Suitable diluents for carrying out theprocess according to the invention are water and organic solvents. Theseinclude in particular aliphatic, alicyclic or aromatic, optionallyhalogenated hydrocarbons, such as, for example, benzine, benzene,toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether,hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride;ethers, such as diethyl ether, diisopropyl ether, dioxan,tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycoldiethyl ether; ketones, such as acetone, butanone or methyl isobutylketone; nitriles, such as acetonitrile, propionitrile or benzonitrile;amides, such as N,N-dimethylformamide, N,N-dimethylacetamide,N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorictriamide; esters such as methyl acetate or ethyl acetate, sulphoxides,such as dimethyl sulphoxide, alcohols, such as methanol, ethanol, n- ori-propanol, ethylene glycol, ethylene glycol monomethyl ether, ethyleneglycol monoethyl ether, diethylene glycol monomethyl ether, diethyleneglycol monoethyl ether, their mixtures with water or pure water.

If appropriate, the process according to the invention is carried out inthe presence of a catalyst. Examples include 4-dimethylaminopyridine,1-hydroxy-benzotriazole and dimethylformamide.

When carrying out the process according to the invention, the reactiontemperatures may be varied within a relatively wide range. In general,temperatures between -20° C. and +200° C., preferably temperaturesbetween 0° C. and 150° C., are employed.

In the practice of the process according to the invention, generally 1to 5 mol, preferably 1.0 to 2.5 mol, of amine are employed per mole ofcarboxylic acid derivative of the formula (II).

The reaction is carried out and reaction products are worked up andisolated according to known processes (cf. the Preparation Example).

The process according to the invention may also be carried out as atwo-step process. For this purpose, the carboxylic acid derivatives ofthe general formula (II) are initially converted into an activated formand reacted with the amines of the general formula (III) in a subsequentstep to give the iminoacetamides of the general formula (I) according tothe invention.

Suitable activated forms of the carboxylic acid derivatives of theformula (II) are all carboxy-activated derivatives, such as, forexample, acyl halides, preferably acyl chlorides, acyl azides, furthersymmetric and mixed anhydrides, such as, for example, the mixedO-alkylcarbonic anhydrides, furthermore activated esters, such as, forexample, p-nitrophenyl esters or N-hydroxysuccinimide esters and adductswith condensing agents, such as, for example, dicyclohexylcarbodiimideor activated forms of the carboxylic acids prepared in situ.

The active compounds according to the invention have potent microbicidalactivity and may be employed in practice for controlling undesirablemicroorganisms. The active compounds are suitable for use as cropprotection agents, in particular as fungicides.

Fungicides are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi orPeronospora brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres orPyrenophora graminea

(conidial form: Drechslera, synonym: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(conidial form: Drechslera, synonym: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for-controlling plant diseases permits thetreatment of aerial parts of plants, of propagation stock and seeds, andof the soil.

The active compounds according to the invention can be employedparticularly successfully for controlling diseases in viticulture,fruit-growing and vegetable-growing, for example against Plasmoparaspecies and Phytophthora species. They can also be employed verysuccessfully for controlling rice diseases, for example Pyriculariaspecies.

Depending on their particular physical and/or chemical properties, theactive compounds are converted into the customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cold and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. In the case of the use of water as an extender, organicsolvents can, for example, also be used as auxiliary solvents.Essentially, the following are suitable as liquid solvents: aromaticssuch as xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water; liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, or else butane, propane,nitrogen and carbon dioxide; suitable solid carriers are: for example,ground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example, crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample, nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or,in their formulations, also as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides in order thus, forexample, to widen the spectrum of action or to prevent development ofresistance. In many cases, synergistic effects are achieved, i.e. theactivity of the mixture is greater than the activity of the individualcomponents.

In many cases synergistic effects are observed.

Particularly advantageous examples of co-components for mixtures are thefollowing compounds:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxy-phenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

dichlorophen, diclobutrazol, diclofluanid, diclomezine, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine,drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione,isoprothiolane, kasugamycin, copper preparations such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb,maneb, mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb,methfuroxam, metiram, metsulfovax, myclobutanil, nickeldimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxycarboxin,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin,polyoxin, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,pyroquilon,

quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thicyofen, thio-phanate-methyl, thiram, tolclophos-methyl, tolylfluanid,triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole,tridemorph, triflumizole, triforine, triticonazole,

validamycin A, vinclozolin,

zineb, ziram.

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides

abamectin, abamectin, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin,

Bacillus thuringiensis, 4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile,bendiocarb, benfuracarb, bensultap, betacyluthrin, bifenthrin, BPMC,brofenprox, bromophos A, bufencarb, buprofezin, butocarboxin,butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chloretoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos,N-[(6-chloro-3-pyridinyl)-methyl]-N'-cyano-N-methyl-ethanimidamide,chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin, clofentezine,cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,

edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etofenprox, etrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb,fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate,fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron,flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos,formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion,ivemectin,

lamda-cyhalothrin, lufenuron,

malathion, mecarbam, mervinphos, mesulfenfos, metaldehyde, methacrifos,methamidophos, methidathion, methiocarb, methomyl, metolcarb,milbemectin, monocrotophos, moxidectin,

naled, NC 184, nitenpyram

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalone,phosmet, phosphamdon, phoxim, pirimicarb, pirimiphos M, primiphos A,profenofos, profenophos, promecarb, propaphos, propoxur, prothiofos,prothiophos, prothoate, pymetrozin, pyrachlophos, pyraclofos,pyraclophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben,pyrimidifen, pyriproxifen,

quinalphos,

salithion, sebufos, silafluofen, sulfotep, sulprofos,

tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin,temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb,thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,triarathene, triazophos, triazuron, trichlorfon, triflumuron,trimethacarb,

vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active compounds, such as herbicides, orfertilizers and growth regulators, is also possible.

The active compounds according to the invention can be used as such orin the form of their commercially available formulations or the useforms prepared therefrom, such as ready-to-use solutions, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, foaming, brushing on and the like. Ifappropriate, the active compounds are applied by the ultra-low volumemethod, or the active compound formulation, or the active compounditself, are injected into the soil. The seeds of the plants can also betreated, if appropriate.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001% by weight.

In the treatment of seed, amounts of active compound of from 0.001 to 50g, preferably 0.01 to 10 g, are generally required per kilogram ofseeds.

In the treatment of the soil, active compound concentrations of from0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight,are required at the treatment site.

PREPARATION EXAMPLES Example 1 ##STR9##

5.5 g (0.015 mol) of ethyl2-(4-chlorophenylimino)-2-(4-bromophenyl)-acetate, 2.72 g (0.015 mol) of2-(3,4-dimethoxyphenyl)-ethylamine and 5.4 g (0.03 mol) of 30% strengthmethanolic sodium methoxide solution in 30 ml of methanol are heated toboiling for 18 hours. The solvent is distilled off and the residue istaken up in dichloromethane and washed successively with 1 Nhydrochloric acid and water, and the organic phase is dried over sodiumsulphate. The solvent is distilled off under reduced pressure and theresidue is chromatographed over silica gel using petroleum ether/ethylacetate (3:1). 2.5 g (33% of theory) of a mixture of e andz-N-[2-(3,4-dimethoxyphenyl)-ethyl]-2-(4-chlorophenylimino)-2-(4-bromophenyl)-acetamideare obtained as an oil.

¹ H NMR (CDCl₃, TMS): δ (ppm)=3.87 (s, 3H).

By a method similar to Example 1, and according to the procedures of thegeneral description of the process, the compounds of the formula (Ie)mentioned in Table 6 below are obtained.

                                      TABLE 6                                     __________________________________________________________________________                                        (Ie)                                                                            #STR10##                                   -                                                                          Ex.                                                                             No. R.sup.5 R.sup.6 R.sup.2 E/Z physical data                               __________________________________________________________________________    2  4-C.sub.2 H.sub.5                                                                    H  CH(CH.sub.3).sub.2                                                                        E/Z                                                                              *)1H NMR: 1.10 (d,3H)                                - 3 4-C.sub.2 H.sub.5 H                                                                                  E/Z *)1H NMR: 3.87 (s,3H)                          - 4 4-Cl H                                                                                               Z log P: 4.32                                      - 5 4-CH.sub.3 H                                                                                         Z *)1H NMR: 3.87 (s,3)                             - 6 --(CH.sub.2).sub.4 --**                                                                              Z *)1H NMR: 3.87 (s,3H)                            - 7 4-Cl H                                                                                               E/Z *)1H NMR: 3.87 (s,3H)                          - 8 4-Cl H                                                                                               E/Z *)1H NMR: 3.88 (s,3H)                          - 9 4-C.sub.2 H.sub.5 H                                                                                  E/Z mp.: 71-72° C.                          - 10 4-C.sub.2 H.sub.5 H                                                                                 E/Z *)1H NMR: 3.87 (s,3H)                          - 11 4-C.sub.2 H.sub.5 H                                                                                 E/Z *)1H NMR: 3.73 (s,3H)                          - 12 4-Br H                                                                                              E/Z *)1H NMR: 3.87 (s,3H)                          - 13 --(CH.sub.2).sub.3 --** H                                                                           Z *)1H NMR: 3.88 (s,3H)                            - 14 --(CH.sub.2).sub.4 -- **                                                                            E/Z *)1H NMR: 3.86 (s,3H)                          - 15 4-CH.sub.3 H                                                                                        E/Z *)1H NMR: 3.86 (s,3H)                          - 16 4-Br H                                                                                              E/Z *)1H NMR: 3.87 (s,3H)                          - 17 4-Br H                                                                                              E/Z *)1H NMR: 3.88 (s,3H)                          - 18 --(CH.sub.2).sub.3 --**                                                                             E/Z *)1H NMR: 3.75 (s,3H)                          - 19 --(CH.sub.2).sub.3 --**                                                                             E/Z *)1H NMR: 3.86 (s,3H)                          - 20 --(CH.sub.2).sub.4 --**                                                                             E/Z *)1H NMR: 3.88 (s,3H)                          - 21 4-Br H                                                                                              E/Z *)1H NMR: 3.88 (s,3H)                          - 22 4-CH.sub.3 H                                                                                        E/Z mp.: 73-74° C.                          - 23 4-CH.sub.3 H                                                                                        E/Z *)1H NMR: 2.19 (s,3H)                          - 24 4-Cl H                                                                                              E/Z mp.: 137° C.                            - 25 4-Cl H                                                                                              E/Z mp.: 122° C.                            - 26 --(CH.sub.2).sub.3 --**                                                                             E/Z *)1H NMR: 3.87 (s,3H)                          - 27 --(CH.sub.2).sub.3 --**                                                                             E/Z *)1H NMR: 3.88 (s,3H)                          - 28 --(CH.sub.2).sub.3 --**                                                                             E/Z *)1H NMR: 3.87 (s,3H)                          - 29 4-Br H                                                                                              E/Z *)1H NMR: 3.89 (s,3H)                       __________________________________________________________________________     *)The 1H NMR spectra were recorded in deuterochloroform (CDCl.sub.3) or       hexadeuterodimethyl sulphoxide (DMSOd.sub.6) using tetramethylsilane (TMS     as internal standard. The chemical shift is given as d value in ppm.          **)In each case attached in positions 3 and 4.                           

Use Examples Example A

Phytophthora test (tomato)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound. After the spray coating has dried on,the plants are inoculated with an aqueous suspension of spores ofPhytophthora infestans.

The plants are placed in an incubation cabinet at a relative atmospherichumidity of 100% and approximately 20° C.

Evaluation is carried out 3 days after the inoculation.

In this test, for example the following compounds (1), (6), (7), (16),(17), (18) and (24) of the preparation examples exhibit, at an activecompound concentration of 50 ppm, an efficacy of up to 98%.

We claim:
 1. Compounds of the general formula (I) ##STR38## in which Arepresents a single bond or optionally substituted alkylene,Q representsoxygen or sulphur, R¹ represents respectively optionally substitutedcycloalkyl, cycloalkenyl, aryl or heterocyclyl, R² representsrespectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl,cycloalkenyl, aryl or heterocyclyl, R³ represents hydrogen orrespectively optionally substituted alkyl, alkenyl, alkinyl orcycloalkyl, R⁴ represents respectively optionally substitutedcycloalkyl, cycloalkenyl, aryl or heterocyclcyl.
 2. Compounds of theformula (I) according to claim 1, in whichA represents a single bond orrepresents alkylene having 1 to 6 carbon atoms which is optionally mono-or polysubstituted by identical or different substituents, thesubstituents being selected from the group consisting of:halogen, cyano,nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl;respectively straight-chain or branched, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms; respectively straight-chain or branched alkenyl or alkenyloxyhaving in each case 2 to 6 carbon atoms; respectively straight-chain orbranched, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl orhalogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to13 identical or different halogen atoms; respectively straight-chain orbranched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 6 carbonatoms in the individual alkyl moieties; cycloalkyl having 3 to 6 carbonatoms; and aryl or heterocyclyl, each of which is optionally mono- orpolysubstituted by identical or different substituents selected from thegroup consisting of: halogen, cyano and/or straight-chain or branchedalkyl having 1 to 4 carbon atoms; and/or straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms; and/or straight-chain or branched alkoxy oralkylthio having 1 to 4 carbon atoms; and/or straight-chain or branchedhalogenoalkoxy or halogenoalkylthio having 1 to 4 carbon atoms and 1 to9 identical or different halogen atoms; and/or respectively doublyattached alkylene or dioxyalkylene having in each case 1 to 6 carbonatoms, each of which is optionally mono- or polysubstituted by identicalor different substituents from halogen and/or straight-chain or branchedalkyl having 1 to 4 carbon atoms and/or straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms; Q represents oxygen or sulphur, R¹ representsaryl, cycloalkyl or cycloalkenyl having 3 to 7 carbon atoms, orheterocyclyl having 3 to 12 ring members, each of which is optionallymono- or polysubstituted by identical or different substituents, thesubstituents being selected from the group consisting of:halogen, cyano,nitro, amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl;respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 8 carbonatoms; respectively straight-chain or branched alkenyl or alkenyloxyhaving in each case 2 to 6 carbon atoms; respectively straight-chain orbranched halogenoalkyl, halogenoalkoxy, halogenoalkylthio,halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1to 6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms; respectively straight-chain orbranched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy,alkoxycarbonyl, alkylsulphonyloxy, hydroxyiminoalkyl or alkoxyiminoalkylhaving in each case 1 to 8 carbon atoms in the individual alkylmoieties; respectively doubly attached alkylene or dioxyalkylene havingin each case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by halogen and/or straight-chain or branched alkylhaving 1 to 4 carbon atoms and/or straight-chain or branchedhalogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical ordifferent halogen atoms; cycloalkyl having 3 to 6 carbon atoms; andaryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of:halogen, cyano and/orstraight-chain or branched alkyl having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms; and/or straight-chain orbranched alkoxy or alkylthio having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkoxy or halogenoalkylthio having 1to 4 carbon atoms and 1 to 9 identical or different halogen atoms;and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms; R² represents alkyl having 1 to 4 carbonatoms, alkenyl or alkinyl having in each case 2 to 4 carbon atoms, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen, cyano,hydroxyl, amino, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl and Cl-C₄ -alkylsulphonyl (each of which is optionallysubstituted by halogen) and optionally substituted phenyl,or representsaryl, cycloalkyl or cycloalkenyl having 3 to 7 carbon atoms, orheterocyclyl having 3 to 12 ring members, each of which is mono- orpolysubstituted by identical or different substituents, the substituentsbeing selected from the group consisting of:halogen, cyano, nitro,amino, hydroxyl, formyl, carboxy, carbamoyl, thiocarbamoyl; respectivelystraight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl oralkylsulphonyl having in each case 1 to 8 carbon atoms; respectivelystraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; respectively straight-chain or branchedhalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinylor halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1to 13 identical or different halogen atoms; respectively straight-chainor branched halogenoalkenyl or halogenoalkenyloxy having in each case 2to 6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy,hydroxyiminoalkyl or alkoxyiminoalkyl having in each case 1 to 8 carbonatoms in the individual alkyl moieties; respectively doubly attachedalkylene or dioxyalkylene having in each case 1 to 6 carbon atoms, eachof which is optionally mono- or polysubstituted by identical ordifferent halogens and/or straight-chain or branched alkyl having 1 to 4carbon atoms and/or straight-chain or branched halogenoalkyl having 1 to4 carbon atoms and 1 to 9 identical or different halogen atoms, R³represents hydrogen or alkyl having 1 to 4 carbon atoms, R⁴ representsaryl, cycloalkyl or cycloalkenyl having 3 to 8 carbon atoms, orheterocyclyl having 3 to 12 ring members, each of which is optionallymono- or polysubstituted by identical or different substituents, thesubstituents being selected from the group consisting of:halogen, cyano,nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl;respectively straight-chain or branched alkyl, alkoxy, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbonatoms; respectively straight-chain or branched alkenyl or alkenyloxyhaving in each case 2 to 6 carbon atoms; respectively straight-chain orbranched halogenoalkyl, halogenoalkoxy, halogenoalkylthio,halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1to 6 carbon atoms and 1 to 13 identical or different halogen atoms;respectively straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13identical or different halogen atoms; respectively straight-chain orbranched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy,alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkylhaving in each case 1 to 6 carbon atoms in the individual alkylmoieties; respectively doubly attached alkylene or dioxyalkylene havingin each case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms; cycloalkyl having 3 to 6 carbon atoms; andaryl, aryloxy, arylthio, arylalkyl, arylalkyloxy, arylalkylthio,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl,heterocyclylalkyloxy or heterocyclylalkylthio, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents selected from the group consisting of:halogen, cyano and/orstraight-chain or branched alkyl having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and1 to 9 identical or different halogen atoms; and/or straight-chain orbranched alkoxy or alkylthio having 1 to 4 carbon atoms; and/orstraight-chain or branched halogenoalkoxy or halogenoalkylthio having 1to 4 carbon atoms and 1 to 9 identical or different halogen atoms;and/or respectively doubly attached alkylene or dioxyalkylene having ineach case 1 to 6 carbon atoms, each of which is optionally mono- orpolysubstituted by identical or different halogens and/or straight-chainor branched alkyl having 1 to 4 carbon atoms and/or straight-chain orbranched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms.
 3. Compounds of the formula (I) according toclaim 1, in whichA represents a single bond or represents methylene,1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-,1,2-, 1,3-, 1,4-, 2,2- or 2,3-butylene or 1,1-, 1,2- or1,3-(2-methylpropylene), each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, cyano and methoxy, Q represents oxygenor sulphur, R¹ represents respectively optionally mono- totrisubstituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl,benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl,pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl,pyrrolidinyl, piperidinyl or morpholinyl, the substituents beingselected from the group consisting of:fluorine, chlorine, bromine,cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl; respectively doubly attached trimethylene(propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl;cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; phenyl, benzyl,phenoxy, benzyloxy, each of which is optionally substituted by theabovementioned substituents; R² represents methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl or propargyl or allyl,or representsrespectively optionally mono- to trisubstituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl, phenyl, naphthyl, furyl, benzofuranyl,pyrrolyl, indolyl, thienyl, benzothienyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, quinolyl,pyrimidyl, pyridazinyl, pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl,perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, thesubstituents being selected from the group consisting of:fluorine,chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxy,carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinylor trifluoromethylsulphonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethylamino, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl; respectively doubly attached trimethylene(propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl; orrepresents benzyl which is substituted the abovementioned substituents,R³ represents hydrogen or represents methyl or ethyl, R⁴ representsoptionally mono- to trisubstituted cyclopropyl, cyclobutyl, cyclopentylor cyclohexyl, phenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl,thienyl, benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl,pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl,pyrrolidinyl, piperidinyl or morpholinyl, the substituents beingselected from the group consisting of:fluorine, chlorine, bromine,cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl,propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyloxy, ethylsulphonyloxy, hydroxyiminomethyl,hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl,methoxyiminoethyl or ethoxyiminoethyl; respectively doubly attachedtrimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl),methylenedioxy or ethylenedioxy, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- andi-propyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. 4.Compounds of the formula (I) according to claim 1, in whichA representsa single bond or represents methylene, 1,1-ethylene, 1,2-ethylene 1,1-,1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butyleneor 1,1-, 1,2- or 1,3-(2-methyl-propylene), each of which is optionallymono- or polysubstituted by identical or different substituents from thegroup consisting of fluorine, chlorine, cyano and methoxy, Q representsoxygen or sulphur, R¹ represents respectively optionally mono- tohexasubstituted cyclobutyl, cyclopentyl or cyclohexyl, the substituentsbeing those listed below;represents respectively optionally mono- totrisubstituted phenyl, naphthyl, furyl, benzofuranyl, thienyl,benzothienyl, pyridyl, quinolyl, tetrahydrofuryl or perhydropyranyl, thesubstituents being selected from the group consisting of: fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-,s- or t-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl, trifluoromethyl,trifluoroethyl, difluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyloxy, ethylsulphonyloxy,hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl,ethoxyiminomethyl, methoxyiminoethyl or ethoxyiminoethyl; respectivelydoubly attached trimethylene (propane-1,3-diyl), tetramethylene(butane-1,4-diyl), methylenedioxy or ethylenedioxy, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, methyl,trifluoromethyl, ethyl, n- and i-propyl; cyclopropyl, cyclopentyl,cyclohexyl; phenyl, phenoxy, benzyloxy, each of which is optionallysubstituted by the abovementioned substituents; R² represents methyl,ethyl, n-, i-propyl, n-, i-, s- or t-butyl, allyl,or representsrespectively optionally mono- to hexasubstituted cyclobutyl, cyclopentylor cyclohexyl, the substituents being those listed below;or representsrespectively optionally mono- to trisubstituted phenyl, naphthyl, furyl,benzofuranyl, thienyl, benzothienyl, pyridyl, quinolyl, tetrahydrofurylor perhydropyranyl, the substituents being selected from the groupconsisting of: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl,n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, n-hexyl, n-heptyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl, trifluoromethylsulphonyl, acetyl, propionyl,acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy,ethylsulphonyloxy, hydroxyiminomethyl, hydroxyiminoethyl,methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl orethoxyiminoethyl; respectively doubly attached trimethylene(propane-1,3-diyl), tetramethylene (butane-1,4-diyl), methylenedioxy orethylenedioxy, each of which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting offluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, orrepresents benzyl which is substituted by the abovementionedsubstituents, R³ represents hydrogen or represents methyl, R⁴ representsrespectively optionally mono- to hexasubstituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, the substituents being thoselisted below;represents respectively optionally mono- to trisubstitutedphenyl, naphthyl, furyl, benzofuranyl, pyrrolyl, indolyl, thienyl,benzothienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,oxadiazolyl, thiadiazolyl, pyridyl, quinolyl, pyrimidyl, pyridazinyl,pyrazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl,pyrrolidinyl, piperidinyl or morpholinyl, the substituents beingselected from the group consisting of:fluorine, chlorine, bromine,cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl,propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyloxy, ethylsulphonyloxy, hydroxyiminomethyl,hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl,methoxyiminoethyl or ethoxyiminoethyl; respectively doubly attachedtrimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl),methylenedioxy or ethylenedioxy, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- andi-propyl; cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. 5.Compounds of the formula (I) according to claim 1, in whichA representsa single bond or represents methylene, 1,1-ethylene, 1,2-ethylene,1,1-propylene, 1,2-propylene, 1,3-propylene or 2,2-propylene, Qrepresents oxygen, R¹ represents phenyl, thienyl or furanyl, each ofwhich is optionally mono- or disubstituted by bromine, chlorine,fluorine, nitro, methylsulphonyl, phenyl, phenyloxy, benzyloxy,cyclopropyl, cyclohexyl, methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, n-pentyl, n-hexyl, n-heptyl, methoxy, ethoxy, trifluoromethyl,trifluoromethoxy and/or methylthio, or represents phenyl which issubstituted by 3,4-methylene- and ethylenedioxo, propane-1,3-diyl andbutane-1,4-diyl, each of which is optionally substituted by fluorine, orrepresents naphthyl, benzofuranyl or benzothienyl, R² represents methylor ethyl, represents n- or i-propyl, represents n-, i-, s- or t-butyl,allyl, cyclopentyl, cyclohexyl or represents optionally chlorine-,methyl- or methoxy-substituted phenyl or benzyl, R³ represents hydrogenor methyl, R⁴ represents cyclohexyl or optionally mono- totrisubstituted phenyl, thienyl, furyl, benzofuryl, benzothienyl,pyridyl, pyrimidinyl, naphthyl, quinolyl, the substituents beingselected from the group consisting of:fluorine, chlorine, bromine,cyano, nitro, amino, hydroxyl, formyl, carboxy, carbamoyl,thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy,trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy,difluoromethylthio, difluorochloromethylthio, trifluoromethylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino,ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl,propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl,methylsulphonyloxy, ethylsulphonyloxy, hydroxyiminomethyl,hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl,methoxyiminoethyl or ethoxyiminoethyl, respectively doubly attachedtrimethylene (propane-1,3-diyl), tetramethylene (butane-1,4-diyl),methylenedioxy or ethylenedioxy, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- andi-propyl.
 6. Process for preparing pesticides, characterized in thatcompounds of the formula (I) according to claim 1 are mixed withextenders and/or surfactants.
 7. Process for preparing compounds of theformula (I) according to claim 1, comprising reacting carboxylic acidderivatives of the formula (II) ##STR39## in which R¹, R² and Q are eachas defined in claim 1 andT represents hydroxyl, halogen or alkoxy,arereacted with an amine of the general formula (III), ##STR40## in whichR³, R⁴ and A are each as defined in claim 1, or with a hydrogen halidethereof if appropriate in the presence of an acid acceptor, ifappropriate in the presence of a condensing agent, if appropriate in thepresence of a catalyst and if appropriate in the presence of a diluent.8. A pesticidal composition comprising a pesticidally effective amountof a compound of the formula (I) according to claim 1 or a mixture ofcompounds of the formula (I) and one or more extenders and/or one ormore surfactants.
 9. A method for controlling pests comprising applyingto pests and/or their habitat a pesticidally effective amount of acompound of the formula (I) according to claim 1 or of a mixture ofcompounds of the formula (I).
 10. A process for preparing a pesticidalcomposition according to claim 8 comprising mixing at least one compoundof the formula (I) according to claim 1 and one or more extenders and/orone or more surfactants.